A Girl's Guide to Chicago Read online

  “Have a good day. If I don’t see you before, I’ll see you Thursday.”

  As I walk into the office that morning, I feel like I’m on cloud nine.

  “Well, someone is in a good mood for a Monday.”

  I sit down across from James at his desk. “Well, someone has a date with “Train Boy” on Thursday.”

  He stops typing on his computer and looks at me. “Ooooh seriously? That’s great! Good for you!”

  “I really need to stop calling him “Train Boy.” Knowing me, I will probably say that to his face.”

  “Yes, you probably will.”

  I roll my eyes at him. “Okay. Well, I just wanted to let you know the good news. We can chat more about it later.”

  I walk to my desk, sit down, and take a big sip of my coffee. All I can think about is how I can’t wait for Thursday.

  I check my email and see one with the subject line, “My Little Chocolate Chip Cookie.” Oh no! What could he want now? I open the email and skim through. My stomach is instantly in knots. He’s coming to Chicago on March 29th for the night, and he wants to go to dinner. I can’t believe it! I don’t want to have dinner with him.

  What do I do? How do I respond? He is a client after all. I feel it would be rude to turn him down. I send an instant message to James.

  OMG! GUESS WHAT! Chocolate Chip Cookie Guy is coming here on March 29th, and he wants to go to dinner!

  He responds with about ten laughing faces.

  James! I’m serious! What should I do?

  I think you just have to suck it up and go to dinner. Kelly, just make sure he knows it’s a business dinner or something. Say that you can go over some project details or something.

  Why do I even have to go?

  Ya don’t. But he’s an important client right now, and with you talking to him so much, you have led him on a little. Don’t you think?

  Maybe. But I wasn’t trying to do that. I was just being nice.

  What did I get myself into! Later that day, I tell Vin what happened with “Chocolate Chip Cookie Guy.” He just starts laughing.

  “I’m really sorry, but it’s kind of your fault. You have been so nice to him. You keep responding to all his emails.”

  “I know! But I’m nice. I'm just nice. I can’t be mean. I thought I was being friendly and doing my job.”

  Toward the end of the day, I respond to “Chocolate Chip Cookie Guy” and tell him that I can do dinner, but I have plans later in the evening. I tell him we can go over some project details, like James suggested, and try to make my email sound as professional as possible. He responds right back with a smiley face and tells me he can’t wait. Oh boy! What on earth did I get myself into!

  I’m sitting in my room on Thursday evening trying to figure out what to wear for my big date. Gracie is hanging out with me exploring my bedroom. My brother is not home, so I can’t ask him. I feel like I haven’t seen David much. He has been working weird hours lately. I don’t even know if he knows I’m going on my date tonight.

  I finally decide to wear a sleeveless top, jeans, heels, and my leather jacket. Spring is almost here in Chicago, so it’s not as freezing anymore. It’s nice not having to wear a sweater and a heavy coat. I’m going from cab to the bar and home again, so I don’t need to be all bundled up. I check my makeup and hair, and I look at my phone. James has sent me a good luck text with a wink face. I respond back with a smiley face as I hear footsteps coming up the stairs.

  The apartment door opens, and David walks in. I run into the living room to greet him. He has a big smile on his face.

  “Good day?”

  “Yeah, it was. I had lunch with one of the directors of the hotel, and he is really impressed with all my hard work and said that next month I can move up to the gym.”

  “Oh my gosh! That’s so exciting! Congratulations! I'm so proud of you!”

  “Thank you! I’m excited about it. You will have to come by and try the gym or one of the classes.”

  “Oh, I definitely will. I’m sure it’s nice. You know . . . I would love to chat more about your job, but I have to leave. I have a date tonight.”

  “Oh, with who?”

  “You remember “Train Boy” I was telling you about? Him.”

  “Really? You actually talked to him.”

  “Yep. We chatted a bit last week and then on Monday he asked me to go out. We are meeting at a wine bar in Lincoln Park.”

  “Wow. Well, have a good time then.”

  “I will! If you are still up when I get home, I will tell you all about it. We can also chat more about your job.”

  “Maybe. But I probably won’t be. I have to be at work early again, but we can talk soon.”

  “Okay, let’s do that. I feel like we haven’t really seen much of each other lately.”

  I give David a huge long hug. I really do miss him. I grab my leather jacket and my bag, slide into my heels, and head out the front door.

  As always when it’s dark out, I walk down the middle of the street, as quickly as I can, in my heels and up to Sheffield to catch a cab. I know I must look like an idiot, but I don’t care. I don’t think I will ever get used to walking in the dark alone. A cab comes along, I get in, and tell him where I’m going. I haven’t been to this area much since dating Dylan. It’s such an adorable area with little boutiques and restaurants.

  Less than ten minutes later, I get out of the cab and head into this quaint little wine bar. Low lighting makes the bar look cozy. There are pretty couches, comfy chairs, and coffee tables. There is a lit tea light candle in the middle of each table. I spot Kevin toward the back of the bar, and he’s sitting in one of two oversized chairs.

  He stands up to greet me with a quick hug.

  “Hi! This place is adorable! Have you ever been here before?” I sit down in the other oversized chair across from him.

  “No. But my roommate has, and he said it is a good place to come for wine. I guess they have a great wine selection.”

  “I can see that.” I quickly glance over the menu.

  We take a few minutes to look over all the choices. We choose a few small plates and two glasses of red wine. It seems as though many restaurants in the city are all about small plates and sharing. I like the idea of it, but I’m not used to choosing what to eat with others, especially with someone I don’t know. I guess it makes dining more intimate and gives you the option to try more things on the menu.

  We enjoy our wine and our small plates and chat about the typical things you talk about on a first date. Where we work. Where we went to school. Where we live. It’s a friendly conversation but not great. I don’t feel like I have found my soulmate. It almost feels like I’m being interviewed. As we finish our wine, he looks over at me.

  “So, how old are you?”

  “Huh?”

  “I’m just wondering. It seems like you have been out of college a little longer than me. You worked in the ’burbs at a preschool before moving here.”

  I’m not ashamed of telling him my age. I’m still young. I’m in my twenties. However, our conversation didn’t seem to flow right all night. I feel like I’m being judged.

  “I’m twenty-six.”

  “Oh. Really? Do you know how old I am?”

  “I don’t know. I figure around the same as me.”

  “I’m twenty-two.”

  “Okay.” I didn’t know what else he wanted me to say and, suddenly, the vibe between us has changed.

  We sit there for a second. I didn’t know how to continue the conversation. Did I really want to date a twenty-two-year-old? Probably not.

  “I think that maybe, maybe umm, you probably want something a little more serious than what I’m looking for. I just moved here from college.”

  “Yep. Okay. I totally get it. I’m not looking to get married tomorrow or anything, but I get what you are saying.”

  The whole conversation has become strange, and I don’t feel like engaging anymore. The server comes by, and Kevin
asks for the bill. It’s nice of him to pay, and he should since he just made the night totally awkward. We stand up to leave and put on our coats.

  “Kelly, I do think you’re really nice. We can still chat on the train, right, and be friends?”

  “Yeah, of course! Totally.” I’m so ready to go home. He keeps making this evening more awkward by the minute.

  I walk out of the bar and, thank goodness, a cab has pulled over, and I get in.

  “Okay, see you on the train! Thank you for the wine and food.”

  “Yep. Good night!”

  As the cab heads down Halsted, I pull out my phone to text James. It’s only 10:03, and he’s probably still up.

  He’s 22.

  Oh, really? No good, you don’t want to date a kid. Next. Tell me more about it tomorrow. Night.

  I take a deep breath, sigh, put my phone back in my bag and look out the window. Oh well. It’s for the best. I was a little bummed since I was so excited to go on this date. Kevin seemed so great. Well, maybe “Chocolate Chip Cookie Guy” will be better. I giggle to myself because I seriously doubt it from his corny emails.

  The next morning at the Fullerton platform, I’m a little nervous to see Kevin. I look around at all the people waiting for the train, but I don’t see him at all. The train pulls into the station. I get on and the doors shut. No more “Train Boy.”

  Twelve

  I walk into work and, of course, the first thing I do is tell the girls about my date with “Train Boy.”

  “Kelly, you should know that once we get to our age, you want to make sure you only date a guy who is mature and established, and someone knows what he wants in life. So, you definitely don't want to date a twenty-two-year-old. An older guy is always the way to go.”

  “Yep. You’re so right, Kourtney.”

  I thought she is somewhat right. Older, yes. Established? I don’t need a guy who already knows everything he wants. I want someone who is my best friend, someone who likes the same things as me. The rest we can figure out together.

  However, I listen as she keeps going one.

  “You know, younger guys are like children, and they just play games. You should always find out his age first and, especially, what they do for a career. You want to make sure he can take care of you. My fiancé is in finance, so I knew he would be able to take care of me. He was just right from the beginning. He . . . ”

  “Oh, can you hold that thought for a second. I think I hear my desk phone.”

  “Oh. Sure. I will be right here. Always happy to give more advice.” She flashes me a smile, and I walk out of the room.

  My desk phone stops ringing, but I see my instant messenger is flashing, and it’s James.

  Do you want to go to this spot called Mercadito after work? I hear they have the best margaritas in the city.

  Yes! Perfect! Just what I need!

  As the day continues, I just can’t shake my bad mood, although I try. I am not looking forward to my date tomorrow night with “Chocolate Chip Cookie Guy.” I have a working lunch with Vin today, but we talk mostly about how his ex-girlfriend keeps calling. She is trying to make him feel bad, and it’s getting him down. I am also in a bad mood about tomorrow night, I tell him.

  “Oh, yeah. Your big date tomorrow.”

  “Stop calling it a date but yep. I feel like I have to go because he is driving all the way here. James said I made him feel as though I’m interested. But, I’m not. Since he is a client, I’m going to go.”

  “Well, you never know until you go. He might just be your dream guy.”

  I roll my eyes at him and take a bite of my salad.

  “You know what?”

  “What?”

  “I’m going to pick you up and drive you tomorrow night. I kind of feel responsible for this “date” since he is a client. You are totally put on the spot. I want to make sure that he’s not crazy. I don’t want to lose my best assistant.”

  “Ha. Ha. Thank you for that, but you really don’t have to. I will be okay. We are meeting at Cafe Ba-Ba-Reeba!”

  “No. I’m picking you up. If you don’t feel comfortable, call me, and I will come get you.”

  “Really?”

  “Really.”

  “Okay, thanks. That is so nice of you.”

  “Of course. What time do you have to be there?”

  “Seven.”

  “Okay. I’ll be by your house around six forty-five. Just text me your address tomorrow.”

  “Okay, I will. Oh, by the way, James said we could all meet at Ann Sather on Sunday. Do you want to come? I think I’m going to invite my brother as well. He doesn’t really know anyone in the city.”

  “Okay, yeah. I’ll come.”

  “Good. I can’t wait to try those cinnamon rolls.

  James and I make it to Mercadito just in time for happy hour. We both order a regular margarita with spicy salt, mango guacamole, and a variety of tacos. James is right about the margaritas. They are strong and delicious. I drink the first one too quickly, and I’m feeling really tipsy after the second.

  Halfway through our meal, I look around Mercadito. It is packed, and the vibe is fun. I like this place. Most of the night, we chat about dating and wonder why guys are always so strange. We share a lot of funny dating stories, which are funnier after a few drinks. My stomach is literally hurting by the end of the night. I start feeling better about tomorrow night. Well, maybe just a little.

  I hang around my apartment all day on Saturday just waiting for tonight. I am not hungover from the margaritas last night, but I spend the day doing nothing. I feel a tad sorry for myself because I have to go on this date tonight, although I know there are way worst things in life. I catch up on the Real Housewives of Beverly Hills and, as I’m watching TV, I receive a few emails from “Chocolate Chip Cookie Guy.” He is excited to come to Chicago and go out to dinner.

  He says he will be at his hotel around four and I can meet him there for a drink before dinner. I tell him I cannot meet before, but I am looking forward to tonight. I feel so guilty for lying. I try to make my email responses sound cheery as I can. I feel like a horrible person, but I seriously have no interest in dating someone from another state. I should have been honest with him from the beginning, then he wouldn’t be coming all the way here.

  I text my address to Vin and ask him if he still wants to drive me tonight. He will be there, he says. It’s forty-five minutes before he is supposed to pick me up, and I’m slowly starting to get ready. I put on a light sweater, jeans, and my new favorite cognac boots. Nothing fancy, just something I typically wear when I go out to dinner with the girls. I lay on my bed and wait for the text from Vin. I tell myself that I am only going out for a few hours. It will be over soon. I can definitely get through this one dinner.

  At six forty-five Vin sends me a text that’s he’s outside. I grab my stuff and head out to meet him. I see a black car and assume it’s his. It’s a beautiful BMW X5, and I tell him that as soon as I open the door and get in.

  “Oh, yeah this thing? I got it a few months ago. I’ve always wanted one.” He is grinning, and I can tell he is proud of his new car.

  “Maybe I can drive it sometime?”

  “Nah.” I look over at him, and he gives me another grin.

  We start driving in the direction of the restaurant. I give a big sigh and lay back in the passenger seat.

  “You really don’t want to go, do you?”

  “No, I don’t, and I feel so bad about all of this.”

  “You should! The guy came all the way here for nothing. You have totally led him on.”

  “I know! I’m such a terrible person, right?”

  “No. You just have to start being more honest with people. It’s okay to say no. You didn’t have to chat with him through emails. You should have kept it professional. That’s what you really should have done.”

  “Yeah, you are so right. I’m so sorry. I wasn't professional at all. I didn’t even think about that. I was just
friendly. I really should have been honest and kept it professional from the beginning.”

  “Well, don’t be too hard on yourself. He should have been more professional as well. But, just go, try to enjoy, and text me if you need anything.”

  We are nearing Cafe Ba-Ba-Reeba! on Halsted, and Vin slows down the car to a stop.

  “Let me know how it goes. I’ll pull over and wait for a few minutes. You can text me that you are okay.”

  “Okay. Thank you so much for driving me.”

  “No problem.”

  I take a deep breath and open the door to the restaurant. It’s packed inside, and I recognize him from his Facebook picture, as he’s looking around anxiously. Alright, it’s just one dinner, and it’s just for a few hours. He spots me walking toward him, grins from ear to ear, and puts out his arms.

  “My little Chocolate Chip Cookie! It’s so nice to finally meet you.”

  “You too!” I give him a big smile and try to sound happy to meet him.

  “Should we go to the bar and have a drink while we wait for our table?”

  “Sure!”

  I follow behind him and quickly pull out my phone to text Vin. I’m okay. We look around for a seat and spot two people getting up from the bar. We head toward them and grab the two stools. I put my jacket over my bar stool and settle in. The bartender hands us two menus, and I take a few minutes to look over the drink list.

  “You know, I’ve never been here before. I’ve heard the food is good. It’s a popular restaurant.”

  “I’ll say! It’s packed in here. I’m surprised we got a seat at the bar.”

  “Yep.” I read the menu to choose what I want to drink. I decide on a glass of red sangria.

  I catch eyes with the bartender, and he asks what we would like to drink. I tell him I want the red sangria and “Chocolate Chip Cookie Guy” orders the same. We chat while we wait for our drinks. Our conversation is a little awkward. We both don’t know what to say. The bartender comes back with our sangrias and asks if we would like any food.

  “Umm, actually, yes we would!”

  I smile at the bartender and turn my seat to face “Chocolate Chip Cookie Guy.” “You know, let’s just eat at the bar since we are already here.”